US9050248B2 - Methods of delivering stable topical drug compositions - Google Patents
Methods of delivering stable topical drug compositions Download PDFInfo
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- US9050248B2 US9050248B2 US13/947,353 US201313947353A US9050248B2 US 9050248 B2 US9050248 B2 US 9050248B2 US 201313947353 A US201313947353 A US 201313947353A US 9050248 B2 US9050248 B2 US 9050248B2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
- A61J3/07—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of capsules or similar small containers for oral use
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K38/02—Peptides of undefined number of amino acids; Derivatives thereof
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
- A61K38/095—Oxytocins; Vasopressins; Related peptides
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- A61K38/11—
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/23—Calcitonins
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/24—Follicle-stimulating hormone [FSH]; Chorionic gonadotropins, e.g. HCG; Luteinising hormone [LH]; Thyroid-stimulating hormone [TSH]
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- A—HUMAN NECESSITIES
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- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/27—Growth hormone [GH] (Somatotropin)
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- A—HUMAN NECESSITIES
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
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- A61K38/55—Protease inhibitors
- A61K38/56—Protease inhibitors from plants
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
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- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
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- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—Insulins
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- Y10S514/806—
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- Y10S514/807—
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- Y10S514/808—
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Definitions
- the present invention relates to topical drug delivery compositions and methods of transdermal drug delivery. More specifically, the present invention relates to stable drug delivery compositions for topical administration.
- Topical drug delivery systems are known. These systems deliver drugs, therapeutic agents and other desired substances transdermally and may be designed to act locally at the point of application or to act systemically once entering the body's blood circulation. In these systems, delivery may be achieved by means such as direct topical application of a substance or drug in the form of an ointment or the like, or by adhesion of a patch with a reservoir or the like that holds the drug and releases it to the skin in a time-controlled fashion.
- Transdermal delivery systems for agents such as drugs, pain relieving compounds, vitamins, and skin improving compounds have been in use for a number of years. These transdermal delivery systems using creams have been developed for use with analgesics and skin refining compounds. Transdermal systems using a patch have been developed for nicotine and estrogen therapies, for instance, estradiol technology described in U.S. Pat. No. 6,521,250 to Meconi, et al.
- a composition for transdermal delivery of a macromolecule comprises a phosphatidylcholine carrier component entrapping the macromolecule, wherein the carrier component stabilizes the macromolecule at room temperature.
- a method for administering a drug or other active agent comprises applying to skin composition containing an effective amount of the drug or active agent, a carrier having a phosphatidylcholine component entrapping the drug or active agent.
- Phosphatidylcholine is used as a carrier for the topical delivery of polypeptides and macromolecules in the practice of this invention.
- Phosphatidylcholine is a basic component of cell membrane bilayers and the main phospholipid circulating in the plasma.
- Phosphatidylcholine is highly absorbable and supplies choline which is needed to facilitate movement of fats and oils across and maintain cell membranes in animals.
- Topical delivery compositions of the present invention are non-polar and formulated to contain polypeptides and macromolecules soluble in phosphatidylcholine, which are then applied to skin for transdermal delivery of the macromolecule.
- Topical delivery compositions of the invention are efficacious in the delivery of macromolecular drugs that are conventionally administered intramuscularly, intravenously or orally, including, but not limited to polypeptides such as insulin and somatropin, prostaglandins, glucocorticoids, estrogens, androgens, and the like.
- topical administration of a composition and transdermal delivery of the drug or active agent therein is easier and pleasanter as an administration route than injections, particularly for drugs such as insulin that must be given to patients over a period of time, or for a lifetime. Furthermore, unlike oral administration where a substantial amount of the drug can be destroyed in the digestive process, the drugs in a topical application are not wasted. Topical application allows a steady diffusion of the drug to the desired target area without the cyclic dosages typical of orally or parenterally administered drugs.
- phosphatidylcholine as used herein means a mixture of stearic, palmitic, and oleic acid diglycerides linked to the choline ester of phosphoric acid, commonly called lecithin.
- lecithin many commercial lecithin products are available, such as, for example, those sold under the tradenames Lecithol®, Vitellin®, Kelecin®, and Granulestin® because lecithin is widely used in the food industry.
- Compositions of the invention can contain synthetic or natural lecithin, or mixtures thereof. Natural preparations are preferred because they exhibit desirable physical characteristics and are both economical and nontoxic.
- Preferred topical delivery compositions of the present invention additionally contain polyenylphosphatidylcholine (herein abbreviated “PPC”) to enhance epidermal penetration.
- PPC polyenylphosphatidylcholine
- the term “polyenylphosphatidylcholine” as used herein means any phosphatidylcholine bearing two fatty acid substituents, wherein at least one is an unsaturated fatty acid with at least two double bonds such as linoleic acid.
- soybean lecithin and soybean fractions for example, contain higher levels of polyenylphosphatidylcholine, with dilinoleoyl-phosphatidylcholine (18:2-18:2 phosphatidylcholine) as the most abundant phosphatidylcholine species, than conventional food grade lecithin, and are useful in formulating topical delivery compositions of the invention.
- conventional soybean lecithin is enriched with polyenylphosphatidylcholine by adding soybean extracts containing high levels of polyenylphosphatidylcholine.
- this type of phosphatidylcholine is called “polyenylphosphatidyl-choline-enriched” phosphatidylcholine (hereinafter referred to as PPC-enriched phosphatidylcholine), even where the term encompasses lecithin obtained from natural sources exhibiting polyenylphosphatidylcholine levels higher than ordinary soybean varieties.
- PPC-enriched phosphatidylcholine polyenylphosphatidyl-choline-enriched phosphatidylcholine
- Rhône-Poulenc's product is a soybean extract containing about 42% dilinoleoylphosphatidylcholine and about 24% palmitoyllinoleylphosphatidylcholine (16:0-18:2 PC) as the major phosphatidylcholine components.
- the PPC-enriched phosphatidylcholine forms a bilayer enveloping the polypeptide or macromolecule to create the topical drug delivery composition, contributing to the stability of the active molecule and enhancing penetration.
- the topical drug delivery composition may be in liquid crystal phase, with the PPC-enriched phosphatidylcholine loosely arranged in multilamellar fashion, with the polypeptide or macromolecule being bonded and entrapped within the lipid bilayers formed therein, as disclosed in U.S. patent application Ser. No. 10/448,632 to Perricone. This forms a loosely arranged, yet stable, PPC-enriched phosphatidylcholine-drug complex that further increases penetration and delivery of the polypeptide or macromolecule to the dermal vasculature.
- Topical drug delivery compositions of the present invention provide an administration route that is a marked improvement over conventional insulin injections, considerably easier and pleasanter. It is a further advantage that compositions of the invention are also stable at room temperature, providing considerable convenience for insulin users who, in the past, have had to deal with the refrigerated insulin products commercially available. Also, insulin compositions according to the present invention have longer shelf lives (whether stored at room temperature or refrigerated) and will not denature at room temperature as would traditional insulin treatments.
- Insulin useful in the topical drug delivery compositions of the present invention is commercially available from a variety of sources, marketed under the tradenames Humulin®, Novolin®, Humalog®, Inutral®, among others. Some of these products contain porcine sequences.
- Compositions of the invention are preferably formulated with recombinant human polypeptides such as those obtained from Sigma Co., Spectrum Chemicals and Laboratories, and similar vendors and employed in the examples that follow. It is an advantage of the invention that topical drug delivery compositions carrying insulin are formulated with commercially available ingredients.
- Topical drug delivery compositions are generally formulated with a carrier comprising a PPC-enriched phosphatidylcholine material with the trade name NAT 8729 (commercially available from vendors such as Rhône-Poulenc and American Lecithin Company) and at least one polyglycol (polyhydric alcohol of a monomeric glycol such as polyethylene glycol (PEG) having molecular weights of 200, 300, 400, 600, 1000, 1450, 3350, 4000, 6000, 8000 and 20000.
- a carrier comprising a PPC-enriched phosphatidylcholine material with the trade name NAT 8729 (commercially available from vendors such as Rhône-Poulenc and American Lecithin Company) and at least one polyglycol (polyhydric alcohol of a monomeric glycol such as polyethylene glycol (PEG) having molecular weights of 200, 300, 400, 600, 1000, 1450, 3350, 4000, 6000, 8000 and 20000.
- PEG poly
- this carrier may comprise a surfactant such as a siloxylated polyether comprising dimethyl, methyl(propylpolyethylene oxide propylene oxide, acetate) siloxane or silicone glycol copolymer fluid commercially available from vendors such as Dow Corning, e.g. poly(oxyehtylene.oxypropylene) methyl polysiloxanne copolymer sold under the tradename Dow Corning 190 surfactant, and lubricant such as silicone fluids containing low viscosity polydimethylsiloxane polymers, methylparaben (p-hydroxy benzoic acid methyl ester) commercially available from vendors such as Down Corning (under the tradename Dow Corning 200 silicone fluid).
- a surfactant such as a siloxylated polyether comprising dimethyl, methyl(propylpolyethylene oxide propylene oxide, acetate) siloxane or silicone glycol copolymer fluid commercially available from vendors such as Dow Corning, e.g. poly(
- purified water may be added to the carrier.
- the carrier is then mixed with a preparation of the particular polypeptide(s) or macromolecule(s) in an amount to obtain the desired strength in the final composition.
- Stable insulin topical preparations were formulated by first preparing a base solution.
- NAT 8729 (45% w/w) was shaved and added to a mixture of polyglycol E200 (50% w/w) and polyglycol E400 (5% w/w) both obtained from Dow Corning.
- the base solution was then covered well and lightning mixed with a special disintegration head impeller slowly at 800 rpm with slight heat. The temperature did not go above 40° C. Typical mixing times were 5 hours.
- the final solution is a crystal clear, viscous amber solution with no sediments or separations.
- the methylparaben was first added to the base solution and mixed for at least an hour until a complete solution formed. Then the Dow Corning 200-5 or 10 cst was slowly added and mixed until a clear solution formed. Afterwards the Dow Corning Fluid 190 was added slowly and mixed into the solution to form the carrier.
- Insulin preparations of the invention were then made using the carrier in two strengths: 50 units and 100 units, by simply dissolving RNA-derived recombinant human insulin obtained from Sigma into the carrier. It was readily soluble in the carrier.
- insulin standards were prepared at 1 mg/ml in 0.01 N HCl using Sigma insulin. (One mg of this material exhibits an activity of 28 insulin units.) Stable insulin compositions samples were prepared at 1 mg/1 ml base by mixing at room temperature for 60 minutes. This mixture was then divided in half, half of which was stored at 4° C., and the other half stored at room temperature. Separation analyses, High Performance Liquid Chromatography (RP-HPLC) and High Performance Capillary Electrophoresis (HPCE), of insulin standards and insulin compositions of the invention which were stored at different temperatures for different periods of time were performed.
- RP-HPLC High Performance Liquid Chromatography
- HPCE High Performance Capillary Electrophoresis
- Stable insulin compositions were formulated by first preparing a base solution.
- Polyglycol E200 (PEG-200) (50% w/w) was weighed and polyglycol E400 (PEG-400) (5% w/w) was added to the same container to obtain the desired weight, (both obtained from Dow Corning).
- PEG-200 and PEG-400 were lightning mixed at 38-40° C. with IKA model RW20 using a disintegration head impeller slowly at 800 rpm (speed 1), yielding PEG-200/PEG-400 solution.
- NAT 8729 containing 80.6% PPC-enriched phosphatidylcholine and 4.9% lysophosphatidylcholine was obtained from Rhône-Poulenc.
- NAT 8729 (45% w/w) was shaved and added to PEG-200/PEG-400 solution, covered and mixed, with temperature not exceeding 40° C., until a clear, viscous amber solution with no sediments or separations resulted. The mixing time was approximately five hours.
- An alternative mixture can be prepared by covering and mixing the solution overnight without heat for a 95-96% yield. The solution was removed from heat and transferred to Ross Homogenizer (Model HSM100LC) using smallest mesh screen.
- Dow Corning Fluid denominated 190 1.00% w/w
- Dow Corning Fluid denoted 200-5 or 10 cst 1.00% w/w
- silicone fluids containing low viscosity polydimethylsiloxane polymers were mixed together in a container with a clean spatula.
- the solution (53.25% w/w) was warmed to 40° C. and mixed at 800 rpm. Typical mixing times were approximately 5 hours. The solution was then milled at 3800 rpm and the Dow Corning Fluid mixture was added very slowly until a clear solution resulted. Methyl Paraben (p-hydroxy benzoic acid methyl ester) obtained from Mallinckrodt (0.75% w/w) was added at once and mixed until a complete solution resulted. Purified water warmed to 40° C. was added very slowly to solution while milling at 7500 rpm for about three minutes. At end of milling, speed was increased to 10,000 rpm for few seconds before stopping. The solution was removed and swept with paddle head using IKA Model RW-20 until cooled to room temperature.
- This step is very critical and if it is not done properly it will generate a biphasic end product.
- the general rule is to use a container having a volume twice that of the solution so the homogenizer head is well embedded in the solution. The solution was then cooled to room temperature.
- USP human recombinant insulin in obtained from Spectrum Chemicals and Laboratories was prepared in 0.01 N HCl at 50 mg/ml, and gently, yet well mixed. This insulin preparation was then added very slowly to the above solution to obtain a final concentration of 500 units/ml or 20 mg/ml. Mixing was continued at room temperature for at least one hour. The final stable insulin composition was stored at 4° C. in amber air-tight container.
- Stable topical drug delivery compositions of the present invention may be employed to deliver and stabilize polypeptides transdermally, including but not limited to insulin, oxytocin, vasopressin, insulin, somatotropin, calcitonin, chorionic gonadotropin, menotropins, follitropins, somatostatins, progestins, and combinations of any of these.
- polypeptides transdermally, including but not limited to insulin, oxytocin, vasopressin, insulin, somatotropin, calcitonin, chorionic gonadotropin, menotropins, follitropins, somatostatins, progestins, and combinations of any of these.
- Somatotropin pituitary growth hormone
- a drug delivery composition formulated with somatotropin was formulated in one trial with 85% phosphatidylcholine to which lipoic acid and ascorbyl palmitate were added. Somatotropin readily dispersed in phosphatidyl-choline and remained stable in it. Growth hormone appeared to penetrate the skin well when the composition was topically applied.
- the present invention may also be used to provide topical delivery of active agents other that drugs, for example, skin care agents.
- the invention is particularly useful with large molecules that are used in some cosmetic formulations, including peptides and polymers.
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US13/947,353 US9050248B2 (en) | 2002-05-31 | 2013-07-22 | Methods of delivering stable topical drug compositions |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38459702P | 2002-05-31 | 2002-05-31 | |
US43727902P | 2002-12-31 | 2002-12-31 | |
US10/448,632 US20040018237A1 (en) | 2002-05-31 | 2003-05-30 | Topical drug delivery using phosphatidylcholine |
US10/749,914 US7182956B2 (en) | 2002-05-31 | 2003-12-31 | Stable topical drug delivery compositions |
US11/334,206 US20060105955A1 (en) | 2002-05-31 | 2006-01-18 | Topical drug delivery using phosphatidylcholine |
US11/344,442 US20060127469A1 (en) | 2002-05-31 | 2006-01-31 | Methods of delivering stable topical drug compositions |
US13/019,101 US20110123577A1 (en) | 2002-05-31 | 2011-02-01 | Method Of Delivering Stable Topical Drug Compositions |
US13/947,353 US9050248B2 (en) | 2002-05-31 | 2013-07-22 | Methods of delivering stable topical drug compositions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US13/019,101 Continuation US20110123577A1 (en) | 2002-05-31 | 2011-02-01 | Method Of Delivering Stable Topical Drug Compositions |
Publications (2)
Publication Number | Publication Date |
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US20130331319A1 US20130331319A1 (en) | 2013-12-12 |
US9050248B2 true US9050248B2 (en) | 2015-06-09 |
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ID=29715338
Family Applications (14)
Application Number | Title | Priority Date | Filing Date |
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US10/448,632 Abandoned US20040018237A1 (en) | 2002-05-31 | 2003-05-30 | Topical drug delivery using phosphatidylcholine |
US10/749,914 Expired - Fee Related US7182956B2 (en) | 2002-05-31 | 2003-12-31 | Stable topical drug delivery compositions |
US11/334,206 Abandoned US20060105955A1 (en) | 2002-05-31 | 2006-01-18 | Topical drug delivery using phosphatidylcholine |
US11/344,442 Abandoned US20060127469A1 (en) | 2002-05-31 | 2006-01-31 | Methods of delivering stable topical drug compositions |
US11/506,137 Abandoned US20060275353A1 (en) | 2002-05-31 | 2006-08-17 | Stable topical drug delivery compositions |
US12/830,857 Abandoned US20100292139A1 (en) | 2002-05-31 | 2010-07-06 | Topical drug delivery using phosphatidylcholine |
US13/019,101 Abandoned US20110123577A1 (en) | 2002-05-31 | 2011-02-01 | Method Of Delivering Stable Topical Drug Compositions |
US13/024,689 Expired - Lifetime US8273711B2 (en) | 2002-05-31 | 2011-02-10 | Topical drug delivery using phosphatidylcholine |
US13/926,688 Abandoned US20130330380A1 (en) | 2002-05-31 | 2013-06-25 | Topical drug delivery using phosphatidylcholine |
US13/947,329 Expired - Fee Related US9060925B2 (en) | 2002-05-31 | 2013-07-22 | Methods of delivering stable topical drug compositions |
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US11/334,206 Abandoned US20060105955A1 (en) | 2002-05-31 | 2006-01-18 | Topical drug delivery using phosphatidylcholine |
US11/344,442 Abandoned US20060127469A1 (en) | 2002-05-31 | 2006-01-31 | Methods of delivering stable topical drug compositions |
US11/506,137 Abandoned US20060275353A1 (en) | 2002-05-31 | 2006-08-17 | Stable topical drug delivery compositions |
US12/830,857 Abandoned US20100292139A1 (en) | 2002-05-31 | 2010-07-06 | Topical drug delivery using phosphatidylcholine |
US13/019,101 Abandoned US20110123577A1 (en) | 2002-05-31 | 2011-02-01 | Method Of Delivering Stable Topical Drug Compositions |
US13/024,689 Expired - Lifetime US8273711B2 (en) | 2002-05-31 | 2011-02-10 | Topical drug delivery using phosphatidylcholine |
US13/926,688 Abandoned US20130330380A1 (en) | 2002-05-31 | 2013-06-25 | Topical drug delivery using phosphatidylcholine |
US13/947,329 Expired - Fee Related US9060925B2 (en) | 2002-05-31 | 2013-07-22 | Methods of delivering stable topical drug compositions |
US13/947,389 Abandoned US20130330381A1 (en) | 2002-05-31 | 2013-07-22 | Methods of delivering stable topical drug compositions |
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US14/705,023 Abandoned US20150238608A1 (en) | 2002-05-31 | 2015-05-06 | Methods of delivering stable topical drug compositions |
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EP (1) | EP1509243B1 (en) |
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CN1671409A (en) | 2005-09-21 |
US20060275353A1 (en) | 2006-12-07 |
IL165480A (en) | 2012-10-31 |
EP1509243A1 (en) | 2005-03-02 |
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CN100509054C (en) | 2009-07-08 |
CA2487305A1 (en) | 2003-12-11 |
US20130330380A1 (en) | 2013-12-12 |
JP2005531595A (en) | 2005-10-20 |
US20130331319A1 (en) | 2013-12-12 |
EP1509243A4 (en) | 2009-06-24 |
ES2632912T3 (en) | 2017-09-18 |
US20130331318A1 (en) | 2013-12-12 |
US20110130330A1 (en) | 2011-06-02 |
US20150004196A1 (en) | 2015-01-01 |
US20040018237A1 (en) | 2004-01-29 |
US8273711B2 (en) | 2012-09-25 |
US20040197391A1 (en) | 2004-10-07 |
US20130330381A1 (en) | 2013-12-12 |
EP1509243B1 (en) | 2017-03-22 |
WO2003101480A1 (en) | 2003-12-11 |
US9060925B2 (en) | 2015-06-23 |
US20150238608A1 (en) | 2015-08-27 |
US20060105955A1 (en) | 2006-05-18 |
US20060127469A1 (en) | 2006-06-15 |
HK1083009A1 (en) | 2006-06-23 |
US20100292139A1 (en) | 2010-11-18 |
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